Pyrido[3,2‐e][1,4] diazepine ‐ Synthese und Prüfung auf Anti‐HIV‐1‐Wirkung

Abstract

Starting from the commercially available 6-methyl-2-pyridylamine (1) the pyrido[3,2-e][1,4]diazepine 14a was synthesized in 12 steps with 7% total yield. 14a, the N-methyl derivative 14b, the thiolactam 15a, the amidine 16, and the 1,2,4-triazole 17 were tested for anti-HIV-1-activity. None of the compounds tested possesses antiviral activity comparable to that of zidovudine (3'-azido-3'-desoxythymidine = AZT).

Synthesis, antimicrobial and antifungal activities of novel 1H-1,4-diazepines containing pyrazolopyrimidinone moiety

“…7 Substituted 1,4-diazepines and their derivatives possess anti-HIV activity. 8 They also showed platelet activating factor (PAF) antagonistic 9 and serotoninergic S 3 antagonistic 10,11 activities.…”

Novel 4-Aroyl-3-alkoxy-2(5H)-furanones as Precursors for the Preparation of Furo[3,4-b][1,4]-diazepine Ring System

“…In recent years some examples of heterocyclic rings fused to the seven member diazepine ring system have been synthesized which exhibit psychotropic activities [2,3,4,5,6,7]. Recently, we have reported on a facile synthesis of novel furodiazepines, namely 7-aryl-4,5-dihydro-2-oxo-3H,8H-furo[3,4-b][1,4]diazepines ( 1 ) using 4-aroyl-3-methoxy-2(5H)-furanones ( 2 ) [1,8].…”

Phenacylation of 6-Methyl-Beta-Nitropyridin-2-Ones and Further Heterocyclization of Products

“…The simplest scheme for the synthesis of 3-and 5-nitro derivatives of 6-methylpyridin-2-one was the diazotation of 2-amino-3(5)-nitro-6-picolines, which, in turn, are available by nitration of commercial 2-amino-6-picoline to 2-nitramino-6-picoline (95%) and its further acidic rearrangement (51%) and steam distillation (leading to 39% of 5-nitro-and 15% of 3-nitropyridin-2-ones). By this way (Scheme 2) both isomers, namely 6-methyl-3-nitropyridin-2-one (1a, yield 32% [11]) and 6-methyl-5-nitropyridin-2-one (1b, yield 25% [12]), were obtained; the low yield at the last step may be due to high solubility of products in acetone for recrystallization.…”

“…6-Methyl-3-and 5-nitropyridin-2-ones (1a,b) were obtained by diazotation of 2-amino-3(5)-nitro-6-picolines [11,12].…”